The study examines possible water savings by replacing alfalfa with winter wheat in the Fergana Valley, located upstream of the Syrdarya River in Central Asia. Agricultural reforms since the 1990s have promoted this change in cropping patterns in the Central Asian states to enhance food security and social benefits. The water use of alfalfa, winter wheat/fallow, and winter wheat/green gram (double cropping) systems is compared for high-deficit, low-deficit, and full irrigation scenarios using hydrological modeling with the HYDRUS-1D software package. Modeling results indicate that replacing alfalfa with winter wheat in the Fergana Valley released significant water resources, mainly by reducing productive crop transpiration when abandoning alfalfa in favor of alternative cropping systems. However, the winter wheat/fallow cropping system caused high evaporation losses from fallow land after harvesting of winter wheat. Double cropping (i.e., the cultivation of green gram as a short duration summer crop after winter wheat harvesting) reduced evaporation losses, enhanced crop output and hence food security, while generating water savings that make more water available for other productive uses. Beyond water savings, this paper also discusses the economic and social gains that double cropping produces for the public within a broader developmental context.